VP of Sales – Enterprise

This is a fully remote position, open to applicants in United States.

📋 Description

• Take charge of the complete sales cycle for national and jumbo employers with over 15,000 employees

• Manage intricate, multi-faceted deals involving stakeholders from HR, Total Rewards, Clinical, and Finance

• Lead the RFP processes, pricing strategies, and contract negotiations

• Establish and nurture relationships with CHROs, Chief Medical Officers, CFOs, and other senior decision-makers

• Create long-term strategic partnerships that align with employer health and wellbeing initiatives

• Navigate and influence relationships with key benefits consulting firms and brokers

• Collaborate across functions to design programs that are optimized both clinically and financially

• Structure multi-year contracts and full-population deployments

• Guide employers towards preventative-first, impactful benefit models

• Collaborate with Customer Success to ensure effective enterprise rollout and activation

• Identify and pursue expansion opportunities within the first 6–9 months post-launch

• Spot and secure growth opportunities across various geographies, populations, and product lines

• Meet quarterly and annual quotas aimed at acquiring 3–4 new enterprise logos each year

• Manage pipeline, forecasting, and deal progression with high precision

• Work with urgency and discipline in a fast-paced, high-growth setting

⛳️ Requirements

• 10–12+ years of experience in enterprise sales within benefits, healthcare, or HR technology

• Proven history of successfully closing large, complex deals with national or jumbo employers

• Established relationships with major consulting firms, including Marsh McLennan, Mercer, WTW, Aon, and Gallagher

• Demonstrated ability to navigate multi-stakeholder, executive-level sales cycles

• Strong commercial acumen, including expertise in pricing strategy, negotiation, and contract structuring

• Capability to work independently as a senior individual contributor while collaborating cross-functionally

• High ownership mindset with a focus on action and results

• Preferred experience in selling preventative health, population health, or clinical programs

• Background in B2B2C or employer-sponsored healthcare models

• Experience in high-growth or venture-backed environments

• Mission-driven with a strong commitment to transforming healthcare

• Thrives in ambiguous and fast-paced situations

• Highly collaborative, with a low ego and team-oriented approach

• Operates with urgency, accountability, and maintains a high standard for excellence

🏝️ Benefits

• Competitive salary and benefits package

• Flexible working hours

• Dynamic work environment that encourages creativity and innovation